Day: April 28, 2021

Reference of 112779-14-3, These common heterocyclic compound, 112779-14-3, name is Ethyl 5-amino-1-(tert-butyl)-1H-pyrazole-4-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Reference Production Example 28-1; Ethyl 5- (lH-pyrrol-1-yl)-l-t-butyl-lH-pyrazole-4- carboxylate; 8.45 g of ethyl 5-amino-l-t-butyl-lH-pyrazole-4- carboxylate was dissolved in 60 ml of acetic acid, and 7.93 g of 2,5-dimethoxytetrahydrofuran was then added. The mixture was heated to reflux for 2 hours. The reaction mixture was concentrated under reduced. pressure. After water was added, the residue was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 8.95 g of ethyl 5-(lH-pyrrol-l-yl)-l-t-butyl-lH-pyrazole-4- carboxylate. 1H-NMR (CDCl3, TMS, 8 (ppm)) : 1.11 (3H, t), 1.46 (9H, s), 4.08 (2H, q), 6.33 (2H, t), 6.70 (2H, t), 7.93 (1H, s)

The synthetic route of 112779-14-3 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 58607-90-2, name is Ethyl 5-oxo-4,5-dihydro-1H-pyrazole-3-carboxylate, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 58607-90-2, Formula: C6H8N2O3

a. PREPARATION OF ETHYL 5-{[r£r-BUTYL(DiMETHYL)siLYL]oxY}-lH- PYRAZOLE-3-CARBO Al). [00552] Tert-butyldimethylsilyl chloride (6.05 g, 40.15 mmol) and imidazole (2.92 g, 42.82 mmol) were added to a stirred solution of ethyl 5-oxo-4,5-dihydro-lH-pyrazole-3- carboxylate (4.18 g, 26.76 mmol) in ACN (90 mL). The mixture was stirred at room temperature for 30 minutes, then diluted with water and extracted with AcOEt. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo to yield ethyl 5- {[tert4outyl(dimethyl)silyl]oxy}-lH-pyrazole-3-carboxylate (3.2 g, 44% yield) as a yellow solid, that was used in the next step without further purification.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 5-oxo-4,5-dihydro-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Adding a certain compound to certain chemical reactions, such as: 67-51-6, name is 3,5-Dimethyl-1H-pyrazole, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 67-51-6, Safety of 3,5-Dimethyl-1H-pyrazole

EXAMPLE 5 Synthesis of 1,3,5-Trimethylpyrazole From 3,5-Dimethylpyrazole The apparatus used was the same as that described in Example 1. 24.03 g of 3,5-dimethylpyrazole, i.e. 0.25 mol, and 4.5 g of dimethyl carbonate, i.e. 0.05 mol, were introduced and the reaction medium was heated to 140 C. and this temperature was maintained throughout the reaction.The dimethyl carbonate was then introduced with a flow rate of 50 mmol/h for 8 hours.The methanol produced was distilled off as it was formed and the excess dimethyl carbonate was also distilled off to stabilize the temperature of the reaction medium at 140 C. After having introduced all the dimethyl carbonate, the reaction medium was allowed to cool to ambient temperature to obtain 15.41 g of 1,3,5-trimethylpyrazole, i.e. 0.14 mol, which corresponded to a yield of 57%. The example which follows does not form part of the invention.It was carried out for the purpose of showing that the continuous withdrawal of the methanol produced during the reaction is necessary to be able to generalize this process to several families of nitrogenous heterocycles and particularly, to nitrogenous heterocycles having a boiling point of less than 190 C.

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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 4-nitro-1H-pyrazole-3-carboxylate

Reference Example 20 Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate A mixture of methyl 4-nitro-1H-pyrazole-3-carboxylate obtained in Reference Example 18 (2.0 g, 11.7 mmol), methyl iodide (2.0 g, 14.0 mmol), potassium carbonate (1.62 g, 11.7 mmol) and acetone (60 mL) was stirred at 30 C. for 5 hr. The mixture was diluted with water, and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 4:1-1:1) to give the title compound, methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate (Rf value 0.43) (0.95 g, yield 44%) and the title compound, methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate (Rf value 0.71) (0.61 g, yield 28%).

The synthetic route of 138786-86-4 has been constantly updated, and we look forward to future research findings.

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 20154-03-4 as follows. Product Details of 20154-03-4

Sodium hydride (60percent suspension in oil, 0.17 g, 4.25 mmol) was washed with hexane, dried under nitrogen and resuspended in dry dimethylformamide (10 mL). 3-trifluoromethyl pyrazole (0.34 g, 2.5 mmol ) was added in one portion. After the gas evolution subsided stirring was continued at room temperature. The (5,11-dihydro-pyrido [2,3-b] [1,5] benzodiazepin-6-yl)- (4-fluoro-2-trifluoromethyl-phenyl)-methanone of Example 4, Step B (0.75 g, 1.94 mmol) was added in one portion and the mixture was placed in an oil bath (preheated at 130°C) overnight. After cooling, the mixture was partitioned between water and ethyl acetate. The organic extracts were dried over sodium sulfate, and evaporated to dryness in vacuo. The residue was crystallized from ethanol to yield the title compound (0.57 g, 57.3percent) as an off-white solid, m.p. 127-129°C. NMR (DMSO-d6, 400 MHz): delta 4.19 and 5.46 (dd, 2H, CONCH2), 6.54 (m, 1H), 6.70 (m, 1H), 6.80 (m, 1H), 7.02 (m, 1H), 7.07 (m, 1H, pyrazole CH), 7.29 (m, 1H), 7.61 (m, 1H), 8.00 (m, 1H), 8.05-8.16 (m, 2H), 8.84 (m, 1H, pyrazole CH), 9.63 (s, 1H, NH) MS (EI, m/z): 503 [M]+ Anal. Calc’d for C24H15F6N5O: C 57.26, H 3.00, N 13.91. Found: C 57.07, H 2.97, N 13.58

According to the analysis of related databases, 20154-03-4, the application of this compound in the production field has become more and more popular.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33146-99-5, name is Dimethyl 1-methyl-1H-pyrazole-3,5-dicarboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Dimethyl 1-methyl-1H-pyrazole-3,5-dicarboxylate

Sodium carbonate (2.14 kg, 20.2 mol) was added to a stirring solution of dimethyl 1 – methyl-1 H-pyrazole-3,5-dicarboxylate (7.95 kg, 40.1 mol) in MeOH (80 L) at 20±5 C. The slurry was stirred for 0.5 h and then filtered. The filter cake was washed with 2-methylTHF (16 L) and then the filtrates were returned to the reactor, followed by 2-methylTHF (24 L). The solution was cooled to 15±3 C and sodium borohydride (3.05 kg, 80.7 mol) was charged in ten portions at 15±3 C. The mixture was stirred for 2 h at 18±3 C after adding NaBH4. It was then quenched by gradually charging acetone (16.4 kg, 283 mol) at 18±3 C, then stirred for 1 h at 20±5 C. Aq. HCI (37 wt%, -8.6 Kg, 87 mol) was then slowly added, keeping the temperature below 30 C, to adjust the pH to 2-3, then the mixture was stirred for 1 h. Saturated aq. Na2CC>3 (~4L) was then slowly added to adjust the pH to 5-6, then the mixture was stirred for 3 h. The mixture was filtered and the filter cake was washed with DCM (16 L). The filtrates were concentrated to approximately 20 L by distillation under reduced pressure, not heating above 40C, then diluted with DCM (40 L) and concentrated again by distilling off solvent (approx. 40 L) under reduced pressure. DCM (80 L) and purified water (32 L) were charged and the resulting mixture was stirred for at least 10 min. The lower (organic) phase was collected and the upper (aqueous) phase was extracted four times with more DCM (40 L per portion). The combined organic phases were concentrated to approximately 20 L by vacuum distillation below 40 C. DCM (80 L) was added and the solution was concentrated again by distilling off solvent (approx. 40 L). The resulting methyl 5-(hydroxymethyl)-1-methyl-1 H-pyrazole-3-carboxylate solution was then diluted with DCM (80 L) and cooled to 10±5 C, whereupon thionyl chloride (4.80 kg, 40.4 mol) was gradually added while keeping the temperature below 15 C. The mixture was then stirred for 1 h at 20±5 C. The mixture was concentrated to not more than 20 L by vacuum distillation below 40 C, then DCM (64 L) and purified water (80 L) were added. After phase separation, the lower (organic) phase was washed twice with aq. Na2CC>3 (9 wt%, 80 L per portion) and then with purified water (80 L). The washed organic phase was concentrated to approximately 14 L by vacuum distillation below 40 C. Two cycles of slowly adding heptane (40 L) and then vacuum distilling to approximately 24 L at below 45 C were then completed. More heptane (40 L) was slowly added and the resulting slurry was stirred at 20±5 C for at least 0.5 h before filtering. The filter cake was washed with heptane (8.0 L) and then dried in a 45 C vacuum oven to give methyl 5-(chloromethyl)-1-methyl-1 H-pyrazole-3- carboxylate (Intermediate 10, 4.87 kg, 64%); m/z (ES+), [M+H]+ = 189. NMR (500 MHz, CDCIs, 27 C) delta 3.91 (s, 3H), 3.99 (s, 3H), 4.59 (s, 2H), 6.82 (s, 1 H).

According to the analysis of related databases, 33146-99-5, the application of this compound in the production field has become more and more popular.

Application of 2458-26-6,Some common heterocyclic compound, 2458-26-6, name is 3-Phenyl-1H-pyrazole, molecular formula is C9H8N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Tert-butyl (S)-(1 -(3-phenyl-1H-pyrazol- 1 -yl)propan-2-yl)carbamate 3-Phenyl-1 H-pyrazole (200 mg, 1 .39 mmol), cesium carbonate (4.52 g, 13.90 mmol) and (S)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate (704 mg, 2.78 mmol) were combined in anhydrous A/,A/-dimethylformamide (4 ml). The resulting suspension was heated to 50 C and the progress of the reaction was monitored by TLC. Once the reaction was complete (~ 3 h) the reaction mixture was quenched by addition of water and the product was extracted with ethyl acetate three times. The organic layers were combined and washed with a saturated aqueous solution of sodium chloride. The crude material was purified by column chromatography, eluting 20% ethyl acetate/petroleum spirits to give the title compound as a colourless solid (183 mg, 44%). LRMS [M+H]+ 302.2 m/z; HRMS [M+H]+ 302.1863 m/z, found 302.1867 m/z; 1H NMR (400 MHz, CDCI3) delta 7.87 – 7.70 (m, 2H), 7.41 – 7.34 (m, 3H), 7.31 – 7.25 (m, 1 H), 6.54 (d, J= 2.3 Hz, 1 H), 5.06 (d, J= 1 .1 Hz, 1 H), 4.25 (dd, J = 13.8, 4.5 Hz, 1 H), 4.20 – 4.10 (m, 1 H), 4.04 (dt, J = 12.4, 6.0 Hz, 1 H), 1 .41 (s, 10H), 1 .12 (d, J = 6.8 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Phenyl-1H-pyrazole, its application will become more common.

Electric Literature of 16034-46-1, The chemical industry reduces the impact on the environment during synthesis 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, I believe this compound will play a more active role in future production and life.

To a solution of 2-methyl-4-(2-phenylethynyl)aniline (50 mg, 226.76 mumol, 1 eq) in pyridine (3 mL) was added T3P (288.60 mg, 453.51 mumol, 269.72 muL, 50%, 2 eq) and 2-methylpyrazole-3-carboxylic acid (28.60 mg, 226.76 mumol, 1 eq). The mixture was stirred at 20 C. for 16 h. The reaction mixture was quenched by addition water (50 mL), extracted with EtOAc (30 mL*3). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue which was purified by preparative HPLC (column: Phenomenex Gemini 150*25 mm*10 um; mobile phase: [water(0.05% HCl)-ACN]; B %: 47%-77%, 10 min) followed by lyophilization to yield 2-methyl-N-[2-methyl-4-(2-phenylethynyl)phenyl]pyrazole-3-carboxamide (compound I-28, 32.57 mg, 92.57 mumol, 40.8% yield, 100% purity, HCl) as a light yellow solid. 1H NMR (400 MHz, CD3OD) delta ppm 7.56-7.49 (m, 3H), 7.47 (s, 1H), 7.42-7.35 (m, 5H), 6.98 (s, 1H), 4.15 (s, 3H), 2.31 (s, 3H); ES-LCMS m/z 316.0 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Methyl-1H-pyrazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 287922-71-8, name is 4-Bromo-1-methyl-1H-pyrazole-3-carbonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 287922-71-8

Example XXXI -Cvano-1 -methyl-1 /-/-pyrazole-4-carboxylic acid a) 500 mg (2.69 mmol) 4-Bromo-1 -methyl-1 H-pyrazole-3-carbonitrile, 1 .21 mg (5.00 muMuomicronIota) Pd(OAc)2, 44.7 mg (0.08 mmol) dppf and 661 mg (8.06 mmol) NaOAc are added to 20 mL MeOH and stirred in an atmosphere of CO (p = 10 bar) at 120 C over night. Then the solvent is removed and the residue is purified by HPLC (MeOH/H2O/TFA). b) 100 mg (0.61 mmol) of the above mentioned product are added to 16 mL of a 1 /1 mixture of MeOH and THF and charged with 0.23 mL (0.91 mmol) of an aq. NaOH solution (c = 4 mol/L). The resulting mixture is stirred at r.t. over night. Then the solvent is removed, water is added to the residue and the solution is acidified with an aq. HCI solution (c = 1 mol/L). The precipitate is filtered off and dried. C6H5N3O2 (M= 151 .1 g/mol) ESI-MS: 152 [M+H]+ Rt (HPLC): 0.45 min (method D)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Synthetic Route of 16617-46-2, These common heterocyclic compound, 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate (1.2 g, 4.60 mmol, 1.20 equiv), 5-amino-lH-pyrazole-4-carbonitrile (400 mg, 3.70 mmol, 1.00 equiv), butan-l-ol (1 mL), and TsOH (10 mg, 0.06 mmol, 0.05 equiv) was stirred for 1 h at 130°C. The reaction progress was monitored by LCMS. The solids were collected by filtration. The solid was washed with 3×1 mL of methanol. This resulted in 0.8 g (71percent) of 5-(3,4-dichlorophenyl)-7-oxo-4H,7H-pyrazolo[l,5-a]pyrimidine-3- carbonitrile as a white solid. *H NMR (300 MHz, DMSO): delta 8.44 (s, 1H), 8.17 (s, 1H), 7.85 (s, 1H), 6.37 (s, 1H)

Statistics shows that 3-Amino-1H-pyrazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 16617-46-2.